Acetic Acid → tert-Butyl 4-{[5-(benzyloxy)-1-(phenylsulfonyl)-1H-indol-4-yl]methyl}piperazine-1-carboxylate

HRID 1159805Notes

Reaction equation

HRID 1159805 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:13]=[CH:12][C:11]=2[C:10]=1[CH:27]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>O>[CH2:1]([O:8][C:9]1[C:10]([CH2:27][N:39]2[CH2:38][CH2:37][N:36]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:41][CH2:40]2)=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:19])=[O:20])[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 866182505-(Benzyloxy)-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde

Product 1

HCID 86618249tert-Butyl 4-{[5-(benzyloxy)-1-(phenylsulfonyl)-1H-indol-4-yl]methyl}piperazine-1-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5-(Benzyloxy)-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde, Intermediate 62 205 mg (0.52 mmol) in dichloroethane[DCE] (10 mL) were added BOC-piperazine, 137 mg (0.74 mmol), NaBH(OAc)3, 333 mg (1.6 mmol) and HOAc, 45 mg (0.8 mmol) and the mixture was stirred at room temperature in sealed test tube over night. Water was added, the phases were separated and the dried (MgSO4) organic phase was evaporated at reduced pressure and the black residue was chromatographed on a column of silica with CHCl3 100% as eluent to yield 260 mg (88%) of a blackish oil. MS (ESI+) for C31H35N3O5S m/z 562 (M+H)+.

Workup

  1. customthe phases were separated
  2. dry with materialthe dried (MgSO4) organic phase
  3. customwas evaporated at reduced pressure
  4. customthe black residue was chromatographed on a column of silica with CHCl3 100% as eluent

Sources & evidence

ORD record
ord-6e3aacdacda54514ac4c15ffdf45bf9a
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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